New oxadiazole/triazole derivatives with antimicrobial and antioxidant properties

• Published in: Journal of molecular structure Vol. 1282; p. 135213
• Main Authors: Dawbaa, Sam, Nuha, Demokrat, Evren, Asaf Evrim, Cankiliç, Meral Yilmaz, Yurttaş, Leyla, Turan, Gülhan
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15.06.2023
• Subjects: Antimicrobial activity; Antioxidant; Molecular dynamics simulation; Oxadiazole; Triazole; Oxadiazole; Triazole; Antimicrobial activity; Molecular dynamics simulation; Antioxidant
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2023.135213

•New series of oxadiazole and triazole derivatives were synthesized.•The new compounds were tested for their antimicrobial and antioxidative properties.•Compounds 7b showed an interesting antimicrobial activity against B. subtilis only.•Compounds 4a and 7a displayed acceptable antioxidative properties.•Molecular docking and molecular dynamics simulation studies were performed. In the search for new antimicrobial agents, we synthesized a new series of oxadiazole and triazole derivatives. The series of N-(benzothiazol-2-yl)-2-{{5-[(2-chlorophenoxy)methyl]-1,3,4-oxadiazol-2-yl}thio}acetamide (4a-4e) and N-(benzothiazol-2-yl)-2-{{5-[(2-chlorophenoxy)methyl]-4-(4-chlorophenyl)-4H-1,2,4-triazol-3-yl}thio}acetamide (7a-7e) derivatized at the C6 of benzothiazole ring were synthesized and tested for their antimicrobial and antioxidant activity. The compounds were analyzed via 1H NMR, 13C NMR, and HRMS. The pharmacokinetic profile of the targeted compounds was predicted via in silico calculations. None of the tested compounds showed promising antibacterial or antifungal activity in comparison to the used reference agents. Compounds 4a and 7a showed some antioxidant potency in comparison to ascorbic acid but their activity did not match exactly that of ascorbic acid. The binding modes for compounds 4a and 7a were revealed and the optimum poses of the compounds in the active site of the tested oxidant enzyme peroxiredoxin 5 (PRDX5) were displayed via a molecular docking study. Molecular dynamics simulation studies for compound 7a showed the key amino acids in the active site of the enzyme and gave information regarding the mechanism of enzyme interaction. DFT calculations were also made for compounds 4a and 7a. [Display omitted]